NDLI: Molecular recognition in anisotropic media. Binding of alkylpyridines to amphiphilic zinc porphyrins incorporated in liposomal bilayer membranes

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Organic & Biomolecular Chemistry Vol - 7 Issue - 6

Organic & Biomolecular Chemistry Vol - 7 Issue - 5

Organic & Biomolecular Chemistry Vol - 7 Issue - 4

Organic & Biomolecular Chemistry Vol - 7 Issue - 3

Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Molecular recognition in anisotropic media. Binding of alkylpyridines to amphiphilic zinc porphyrins incorporated in liposomal bilayer membranes

Content Provider	Royal Society of Chemistry (RSC)
Author	Mizutani, Tadashi Minami, Asuka Murakami, Ryosuke
Copyright Year	2009
Abstract	Two amphiphilic zinc porphyrins were incorporated into liposomal bilayer membranes, egg phosphatidylcholine (Egg PC) and dipalmitoylphosphatidylcholine (DPPC). Binding free energy of alkylpyridines to the zinc porphyrins linearly increased as the length of the alkyl chains of the guest increased, showing that the guest was incorporated deep in the bilayer membranes in a hydrophobic environment. Comparison of the free energy increase per CH2 group indicated that recognition of 3-alkylpyridines were favored over that of 4-alkylpyridines by δΔΔG° = 0.3–0.7 kJ mol−1, and this preference was attributed to the anisotropy of the liposomal bilayer membranes. The binding was exothermic (ΔH° = −15 to −21 kJ mol−1) when the liposome was in a liquid crystalline phase, while it was endothermic (ΔH° = 53 to 62 kJ mol−1) when the liposome was in a gel phase. Local disorder of lipid molecules may be a driving force for binding in the latter case. Lipid bilayer membranes provide a unique medium for molecular recognition, in which the anisotropy and entropy of the lipid molecules add new features to binding.
Starting Page	1437
Ending Page	1444
Page Count	8
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	7
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b817241b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Personal computer Liposome Entropy Hydrophobe Zinc Lipid Endothermic process Exothermic process Anisotropy Alkane Phosphatidylcholine Lipid bilayer Amphiphile Base pair Dipalmitoylphosphatidylcholine
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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